Former après musician Teddy Robb jumpstarted his Nashville country music career at Pepi's Bar |

Former après musician Teddy Robb jumpstarted his Nashville country music career at Pepi’s Bar

Pepi’s Bar is a central spot in Vail Village. With immediately recognizable flower beds and orange umbrellas on the patio, there’s always some sort of magical Vail vibes floating off the infamous deck. Often times too, there’s sound wafting into the streets from musicians playing. Recent musicians have even played to crowds social distancing on Bridge Street.

For country music artist Teddy Robb, Pepi’s brought him a year of living in Vail and his current recording contract. The former local après musician decided he wanted to live here in Pepi’s and decided to take the next step in that same seat a year later. He met Evan Greene, who was the Chief Marketing Director of the Grammy Awards at the time. Over beers and sounds from Robb’s friend and fellow local musician Andy Cyphert, Robb experienced just an inkling of how much his life would change following that meeting.

Robb just released “Heaven on Dirt,” a single that’s in some ways an homage to his time in Vail. Below, Robb tells the story of his year in Vail and how it led to his career as a country artist.

Vail Daily: How did you end up in Vail?

Teddy Robb: Vail was always a place I dreamed about living, ever since I was little. The first time I went to Vail was when I was 17 or 18 on a snowboarding trip with my stepdad and a friend. I fell in love with it. I grew up snowboarding and skiing. I started going on trips every year. In 2014, I was living in Nashville and I went on my snowboarding trip and I went into Pepi’s one evening. We started carrying on one evening, as one does at Pepi’s.

VD: Oh, I’m familiar.

TR: Do you know Dave Tucker?

VD: Yeah.

TR: So Dave Tucker was playing, I didn’t know him at the time. I was just one of the crazy vacationers. My friends bet me, “20 bucks you go up and sing.” I was like, okay. I was in Nashville playing covers down on Broadway for a living. So I give Dave 20 bucks and I say, “hey, can I sing a song?” He said “take a few, I’ve been up here for three hours.” I get up, I sing a few songs, I come off stage and Sheika (Gramshammer) and Matt, who was the manager at the time, said ‘would you want to be one of our house musicians?’ Dave had 4 days a week. I moved out there to get three days a week. Do you know Andy Cyphert?

VD: I do.

TR: So I called him up, we’re both from Ohio and that’s how I know him, I go, “hey Andy, I’ve got this gig out in Colorado, we might have to get some side gigs but I think we can live in Vail for the winter.” Andy agrees, and we show up. We’re a duo at Pepi’s on Monday, Tuesday, Wednesday. We start getting more calls, we’re working our butts off. Soon, we’re playing every night of the week.

VD: That’s awesome because Andy is still a full-time musician out here.

TR: Yeah. We were doing all kinds of stuff. I originally intended to do just winter and move back to Nashville. But everyone says you come for the winter and stay for the summer. So I ended up staying a full year in Vail. It was this moment in time for me that I will always, always remember. As much as it was about the music for me, it was also about the lifestyle. Music just happened to be the way that I was able to support myself. I got to spend this magical year in the mountains. At the end of that time, I started thinking I wanted to get back to Nashville.

VD: And then it all lines up.

TR: Yep. I was actually at Pepi’s, watching Andy play. A group walked in and I could tell they were looking for a table. I had a whole table to myself so I said, “hey, you guys can sit here, I’m getting ready to leave.” Next thing you know, they put a beer down in front of me and we started cutting it up. I told them I knew Andy and I was trying to figure some things out. One of the guys at the table, Evan Greene, he was the CMO of the Grammy Awards. He asked me, “what do you want?” I said, “ultimately, I want to be a country singer. I want to move back to Nahsville and be a recording artist.” He handed me a card and said, “well, I don’t know what I can do, but maybe I can connect some pieces for you.” Which he did. I got connected to a guy named Ben Fowler, who is still my producer today. Ben connected me with Monument Records and I got a record deal not even a year from the time I met Evan. That moment at Pepi‘s started this whole new life for me.

Teddy Robb has released an EP and and a new single so far this year.
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VD: That’s really full circle for your journey in Vail.

TR: Yeah, up to that point it was bar gigs, bar gigs, bar gigs. Learn my craft, figure out my sound, play four-hour gigs. Then I was sitting at Pepi’s on a fateful evening and that was the break I needed to start this whole new journey of becoming a recording artist.

For Teddy Robb, living in Vail in 2014 was a “magical” year that allowed him to live out his childhood dreams.
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VD: Now that you’re several years into your proper career, what does that time in Vail mean to you?

TR: I didn’t see the crazy chance that happened or how amazing that story really was. Being removed from it a few years now, I look back and it brings a smile to my face every time I think about it. Really, my whole year at Vail changed my life forever. I was doing 14ers, I got to go whitewater rafting. I had 80 days on my snowboard, I went camping. I finally got to do this thing that I wanted to do my whole life. I always wanted to move out west.

VD: It’s also almost like an American Dream thing. One of the expert guests in Ken Burns’ “The West” documentary says, ‘when you think about America, you think about the West.’

TR: It’s amazing. I’m a kid from Akron, Ohio. There’s not a lot of country in Akron, Ohio. I grew up watching Western movies and dreaming of doing all that. Vail let me experience those things I’d been dreaming about my whole life.

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